The title compound, C
10H
11ClN
4, also known as acetamiprid, is a potent chemical found to exhibit insecticidal activity. The dihedral angle between the planes passing through the 6-chloropyridine ring and the
N′-cyano-
N-methylimidoformamide moiety is 76.7 (1) Å. The crystal structure is stabilized by C—H
N intermolecular interactions.
Supporting information
CCDC reference: 243118
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.114
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - C9 .. 5.39 su
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 27.44
From the CIF: _reflns_number_total 2336
Count of symmetry unique reflns 1330
Completeness (_total/calc) 175.64%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1006
Fraction of Friedel pairs measured 0.756
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
(
E)—
N1-[(6-Chloropyridin-3-yl)methyl]-
N2-cyano-
N1-methylacetamidine
top
Crystal data top
| C10H11ClN4 | F(000) = 464 |
| Mr = 222.68 | Dx = 1.344 Mg m−3 |
| Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2ac | Cell parameters from 875 reflections |
| a = 8.776 (3) Å | θ = 1.6–25.4° |
| b = 11.780 (5) Å | µ = 0.32 mm−1 |
| c = 10.645 (4) Å | T = 293 K |
| V = 1100.5 (7) Å3 | Prisms, colourless |
| Z = 4 | 0.52 × 0.15 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector
diffractometer | 2336 independent reflections |
| Radiation source: fine-focus sealed tube | 1930 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.023 |
| φ and ω scans | θmax = 27.4°, θmin = 1.7° |
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996) | h = −10→11 |
| Tmin = 0.852, Tmax = 0.970 | k = −14→15 |
| 8291 measured reflections | l = −13→13 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.0103P]
where P = (Fo2 + 2Fc2)/3 |
| S = 1.17 | (Δ/σ)max < 0.001 |
| 2336 reflections | Δρmax = 0.20 e Å−3 |
| 158 parameters | Δρmin = −0.13 e Å−3 |
| 1 restraint | Absolute structure: Flack (1983), 1006 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (8) |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| Cl1 | 0.74763 (9) | 0.33691 (6) | 0.00215 (9) | 0.0805 (3) | |
| N1 | 0.5124 (3) | 0.4264 (2) | 0.1110 (2) | 0.0700 (6) | |
| N2 | 0.1306 (2) | 0.25285 (16) | 0.34870 (19) | 0.0546 (5) | |
| N3 | 0.2313 (2) | 0.15653 (16) | 0.5128 (2) | 0.0563 (5) | |
| N4 | 0.2334 (3) | 0.0021 (2) | 0.6680 (3) | 0.0848 (8) | |
| C1 | 0.6010 (3) | 0.3381 (2) | 0.1134 (2) | 0.0545 (6) | |
| C2 | 0.5879 (3) | 0.2474 (2) | 0.1931 (3) | 0.0583 (6) | |
| C3 | 0.4714 (3) | 0.2497 (2) | 0.2775 (3) | 0.0583 (7) | |
| C4 | 0.3711 (3) | 0.34033 (17) | 0.2802 (2) | 0.0498 (6) | |
| C5 | 0.3992 (3) | 0.4254 (2) | 0.1957 (3) | 0.0672 (7) | |
| C6 | 0.2385 (3) | 0.3453 (2) | 0.3690 (3) | 0.0592 (7) | |
| C7 | 0.0289 (3) | 0.2666 (3) | 0.2416 (3) | 0.0711 (7) | |
| C8 | 0.1284 (3) | 0.16306 (19) | 0.4236 (2) | 0.0514 (6) | |
| C9 | 0.2272 (3) | 0.0714 (2) | 0.5922 (3) | 0.0614 (7) | |
| C10 | 0.0101 (4) | 0.0741 (2) | 0.4030 (3) | 0.0729 (8) | |
| H2 | 0.656 (3) | 0.193 (2) | 0.184 (2) | 0.049 (6)* | |
| H3 | 0.454 (3) | 0.194 (2) | 0.331 (3) | 0.057 (7)* | |
| H5 | 0.334 (3) | 0.484 (2) | 0.196 (3) | 0.066 (7)* | |
| H6B | 0.187 (3) | 0.415 (2) | 0.358 (2) | 0.048 (6)* | |
| H6A | 0.276 (4) | 0.339 (2) | 0.457 (4) | 0.084 (11)* | |
| H7A | 0.0021 | 0.1933 | 0.2089 | 0.107* | |
| H7B | 0.0792 | 0.3100 | 0.1775 | 0.107* | |
| H7C | −0.0617 | 0.3056 | 0.2679 | 0.107* | |
| H10A | 0.0171 | 0.0180 | 0.4682 | 0.109* | |
| H10B | 0.0262 | 0.0387 | 0.3229 | 0.109* | |
| H10C | −0.0891 | 0.1084 | 0.4048 | 0.109* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| Cl1 | 0.0636 (4) | 0.1042 (6) | 0.0736 (4) | −0.0124 (4) | 0.0128 (4) | −0.0106 (5) |
| N1 | 0.0676 (15) | 0.0680 (13) | 0.0745 (15) | 0.0023 (12) | 0.0105 (13) | 0.0141 (12) |
| N2 | 0.0501 (11) | 0.0598 (11) | 0.0538 (11) | 0.0013 (9) | 0.0029 (9) | 0.0017 (10) |
| N3 | 0.0556 (13) | 0.0587 (11) | 0.0547 (13) | −0.0003 (10) | 0.0042 (11) | 0.0050 (11) |
| N4 | 0.0889 (19) | 0.0814 (15) | 0.0842 (19) | 0.0206 (14) | 0.0159 (14) | 0.0250 (15) |
| C1 | 0.0447 (13) | 0.0636 (15) | 0.0554 (14) | −0.0111 (12) | −0.0028 (11) | −0.0068 (12) |
| C2 | 0.0490 (15) | 0.0515 (14) | 0.0745 (17) | 0.0028 (12) | −0.0033 (13) | −0.0039 (12) |
| C3 | 0.0628 (17) | 0.0460 (13) | 0.0660 (18) | −0.0006 (11) | −0.0037 (14) | 0.0082 (13) |
| C4 | 0.0523 (13) | 0.0437 (11) | 0.0534 (15) | −0.0047 (10) | −0.0062 (10) | −0.0043 (11) |
| C5 | 0.0670 (17) | 0.0508 (14) | 0.0838 (19) | 0.0090 (13) | 0.0086 (15) | 0.0099 (13) |
| C6 | 0.0676 (18) | 0.0451 (13) | 0.0649 (18) | 0.0012 (13) | 0.0078 (13) | −0.0052 (12) |
| C7 | 0.0603 (15) | 0.0943 (19) | 0.0586 (16) | 0.0083 (14) | −0.0031 (14) | 0.0020 (15) |
| C8 | 0.0473 (13) | 0.0544 (12) | 0.0526 (13) | 0.0010 (11) | 0.0087 (11) | −0.0068 (11) |
| C9 | 0.0530 (15) | 0.0655 (15) | 0.0658 (16) | 0.0101 (12) | 0.0097 (12) | 0.0030 (14) |
| C10 | 0.0679 (18) | 0.0758 (17) | 0.0751 (18) | −0.0147 (14) | 0.0059 (15) | 0.0001 (15) |
Geometric parameters (Å, º) top
| Cl1—C1 | 1.749 (3) | C2—C1 | 1.370 (4) |
| N3—C9 | 1.312 (4) | C2—H2 | 0.88 (3) |
| N3—C8 | 1.312 (4) | C6—H6B | 0.94 (3) |
| N2—C8 | 1.325 (3) | C6—H6A | 0.99 (4) |
| N2—C7 | 1.457 (4) | C8—C10 | 1.491 (4) |
| N2—C6 | 1.459 (3) | C3—H3 | 0.88 (3) |
| N4—C9 | 1.149 (3) | C10—H10A | 0.9600 |
| C4—C5 | 1.369 (4) | C10—H10B | 0.9600 |
| C4—C3 | 1.384 (3) | C10—H10C | 0.9600 |
| C4—C6 | 1.500 (4) | C5—H5 | 0.90 (3) |
| N1—C1 | 1.298 (3) | C7—H7A | 0.9600 |
| N1—C5 | 1.341 (4) | C7—H7B | 0.9600 |
| C2—C3 | 1.361 (4) | C7—H7C | 0.9600 |
| | | |
| C9—N3—C8 | 119.5 (2) | C2—C3—H3 | 122.5 (18) |
| C8—N2—C7 | 123.4 (2) | C4—C3—H3 | 117.0 (18) |
| C8—N2—C6 | 121.1 (2) | N1—C1—C2 | 125.9 (3) |
| C7—N2—C6 | 115.5 (2) | N1—C1—Cl1 | 115.74 (19) |
| C5—C4—C3 | 115.9 (3) | C2—C1—Cl1 | 118.3 (2) |
| C5—C4—C6 | 121.7 (2) | C8—C10—H10A | 109.5 |
| C3—C4—C6 | 122.5 (2) | C8—C10—H10B | 109.5 |
| C1—N1—C5 | 115.1 (2) | H10A—C10—H10B | 109.5 |
| C3—C2—C1 | 117.1 (3) | C8—C10—H10C | 109.5 |
| C3—C2—H2 | 126.4 (17) | H10A—C10—H10C | 109.5 |
| C1—C2—H2 | 116.4 (17) | H10B—C10—H10C | 109.5 |
| N2—C6—C4 | 112.4 (2) | N1—C5—C4 | 125.5 (3) |
| N2—C6—H6B | 108.5 (14) | N1—C5—H5 | 118.0 (18) |
| C4—C6—H6B | 109.1 (14) | C4—C5—H5 | 116.4 (18) |
| N2—C6—H6A | 107.5 (18) | N2—C7—H7A | 109.5 |
| C4—C6—H6A | 109 (2) | N2—C7—H7B | 109.5 |
| H6B—C6—H6A | 110 (2) | H7A—C7—H7B | 109.5 |
| N3—C8—N2 | 118.2 (2) | N2—C7—H7C | 109.5 |
| N3—C8—C10 | 123.0 (2) | H7A—C7—H7C | 109.5 |
| N2—C8—C10 | 118.8 (2) | H7B—C7—H7C | 109.5 |
| C2—C3—C4 | 120.5 (2) | N4—C9—N3 | 173.7 (3) |
| | | |
| C8—N2—C6—C4 | 101.8 (3) | C1—C2—C3—C4 | 0.4 (4) |
| C7—N2—C6—C4 | −77.7 (3) | C5—C4—C3—C2 | −1.0 (4) |
| C5—C4—C6—N2 | 117.7 (3) | C6—C4—C3—C2 | 178.3 (2) |
| C3—C4—C6—N2 | −61.6 (3) | C5—N1—C1—C2 | 0.0 (4) |
| C9—N3—C8—N2 | 176.7 (2) | C5—N1—C1—Cl1 | 179.1 (2) |
| C9—N3—C8—C10 | −3.4 (4) | C3—C2—C1—N1 | 0.1 (4) |
| C7—N2—C8—N3 | 176.1 (2) | C3—C2—C1—Cl1 | −179.0 (2) |
| C6—N2—C8—N3 | −3.5 (3) | C1—N1—C5—C4 | −0.6 (4) |
| C7—N2—C8—C10 | −3.8 (4) | C3—C4—C5—N1 | 1.2 (4) |
| C6—N2—C8—C10 | 176.6 (2) | C6—C4—C5—N1 | −178.1 (3) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···N4i | 0.90 (3) | 2.48 (2) | 3.345 (4) | 161 (2) |
| Symmetry code: (i) −x+1, −y, z−1/2. |
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![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C) = 0.004 Å
Alert level C
Alert level G
